Preheat the oven to 425 degrees. Line 2 baking sheets with aluminum foil or parchment paper. In a large bowl, add butternut squash, toss with olive oil and 1 Tablespoon maple syrup, salt and pepper. Spread it out on one of the baking sheets. Add Brussel sprouts to the other baking sheet and toss with olive oil, salt and pepper.

Roast butternut squash in the oven for 25 - 30 minutes or until the edges are brown and the center is tender. Add Brussel sprouts to the oven 10 minutes later, roasting them for about 15 - 20 minutes total, until crispy & tender. When butternut squash and brussel sprouts have roasted for about 30 and 20 minutes, respectively, and are done, remove them from the oven.

Serve roasted vegetables in a large bowl or platter. Add pecans, cranberries, and remaining maple syrup and toss. Serve immediately.